Haley Winn: From Childhood Dream to Olympic Glory

Sibling rivalries are a common part of family life, but for Haley Winn, her brothers collectively agree she’s the most athletic member of their family. And it’s easy to see why – she’s representing the United States on the world’s biggest stage at the 2026 Winter Olympics.

“I think it’s pretty obvious,” Tommy Winn, one of Haley’s three older brothers, told USA TODAY Sports. “She’s competing… on the biggest stage in the world, so it’s got to be Haley.”

A Lifelong Pursuit

Becoming an Olympian has been a lifelong goal for Winn, a dream that dates back to her grade school days. A yearbook photo unearthed by Tommy Winn perfectly encapsulates her ambition: “Haley Winn, Hockey Olympian.”

“As long as I can remember, it’s been my dream to be here,” said Winn, who has already made a significant impact in her first Games, recording four points with one goal and three assists, including a crucial assist against Sweden. “But seeing that photo was pretty cool.”

Family Support: A Viral Sensation

Winn isn’t alone in this journey. Her entire family has traveled to Milan to cheer her on, and her three brothers – Casey, Ryan, and Tommy – have taken their support to a whole new level. Their coordinating, and often outlandish, outfits have captivated audiences across the nation, becoming a viral sensation.

The brothers’ dedication is truly remarkable. They donned matching American flag tracksuits and bucket hats for the USA’s 5-0 preliminary win over Switzerland, where Winn scored her first Olympic goal. They channeled vintage paperboys for the 5-0 shutout of Canada, where Winn assisted the game-winning goal. And for the 6-0 quarterfinal rout of Italy, they sported mullet wigs and Americana-inspired attire during Winn’s second assist.

Tommy Winn revealed that most of their patriotic ensembles are sourced from Amazon. Their outfits began at the 2024 World Championships, and have only escalated from there. Their semifinal ensemble – a red, white, and blue onesie featuring stars, stripes, and a bald eagle – complete with a $9.99 bald eagle mask, drew enthusiastic applause from the crowd at Milano Santagiulia Ice Hockey Arena.

“We figured biggest stage of the world, we got to go bigger and better,” Tommy Winn explained. “So we pulled out a new outfit for each game that we went to and we kind of just bounced ideas off each other, saw what we liked, what we didn’t like… It was a collaborative effort.”

A Surprise for Haley

Interestingly, Haley is kept in the dark about her brothers’ outfits. “We told her that we were going to be bringing some crazy outfits, so she was kind of aware. But she wanted all the outfits to be a surprise, so she didn’t know exactly what was coming,” Tommy Winn shared, adding that his sister might be “a little embarrassed” by their exuberant displays.

However, Haley insists she’s anything but embarrassed. “I’m so grateful, obviously, that they’re so passionate and supportive,” she said. “I’m definitely glad that they’re taking more of the social media heat. That’s awesome. But no, I mean no embarrassment that they’re supporting us.”

Gold Medal Dreams

With her family and friends cheering her on, Winn feels “so surreal” to have her Olympic dream become a reality. Now, a gold medal is within reach. Winn and the U.S. women’s hockey team will face off against rival Canada on Thursday in pursuit of their first Olympic gold since 2018.

Winn acknowledges she “wouldn’t be here” without her family. “You’re kind of at a loss of words, obviously. I’m so blessed that they’re here… it’s so special to have those kind of people in your corner.”

Tommy Winn echoed this sentiment, saying watching his sister achieve her goals “means the world to us and to Haley.” “It’s been her dream for as long as I can remember and it honestly turned into my dream just for her to make it here. And it’s a privilege for her to be able to play for the United States, for us to be here and watching. It’s been a great experience.”

A Calmer Look for the Gold Medal Game

In a surprising turn, the Winn brothers have announced a “calmer” look for the gold medal match, prioritizing attention on the athletes. “Obviously we just love supporting Haley and the entire US women’s hockey team, but we want just more eyes reaching them and reaching just women’s sports in general,” Tommy Winn explained. “That gold medal game, we want all eyes on them. So we’re going to keep it calm and most likely just break out some jerseys.”

A true display of big brother support.

Follow USA Today’s National Women’s Sports reporter, Cydney Henderson, on Twitter at @CydHenderson.